Prior to the present invention, attempts to epoxidize olefinically unsaturated organic materials with hydrogen peroxide have met with only limited success. One procedure, is shown by U.S. Pat. No. 2,786,854, based on the use of an inorganic peracid, such as a peracid of tungsten, which proved to be inactive with olefinically unsaturated hydrocarbons. Another procedure is shown by British Pat. No. 1,399,639, directed to a process for epoxidizing olefinically unsaturated compounds with hydrogen peroxide in the presence of a fluorinated ketone and/or fluorinated ketone hydrate. Although improved results were achieved with the use of fluorinated ketones as a catalyst, it was often difficult to obtain fluorinated ketone such as hexafluoroacetone commercially. As a result, the feasibility of employing such catalysts for the hydrogen peroxide epoxidation of olefinically unsaturated organic materials was economically unattractive.
The present invention is based on the discovery that tetrachloroacetone, an inexpensive, commercially available material can be utilized with hydrogen peroxide to effect the epoxidation of a variety of olefinically unsaturated organic materials if utilized in a particular manner in the presence of an inert organic solvent. One procedure, for example, involves the employment of a buffer, such as sodium hydrogen phosphate when utilizing the tetrachloroacetone and the olefinically unsaturated organic material in the presence of an effective amount of the hydrogen peroxide. Another procedure involves the incremental addition of the hydrogen peroxide to the tetrachloroacetone-olefinically unsaturated organic material reaction mixture while it is refluxing. It has been found that the tetrachloroacetone can be recovered and recycled after the epoxidation of the olefinically unsaturated organic material.